WO2010051890A3 - Method for producing mono-vinylfunctionalized dialkylphosphinic acid, salts and esters thereof, and the use thereof - Google Patents

Method for producing mono-vinylfunctionalized dialkylphosphinic acid, salts and esters thereof, and the use thereof Download PDF

Info

Publication number
WO2010051890A3
WO2010051890A3 PCT/EP2009/007130 EP2009007130W WO2010051890A3 WO 2010051890 A3 WO2010051890 A3 WO 2010051890A3 EP 2009007130 W EP2009007130 W EP 2009007130W WO 2010051890 A3 WO2010051890 A3 WO 2010051890A3
Authority
WO
WIPO (PCT)
Prior art keywords
vinylfunctionalized
esters
salts
transition metal
catalyst
Prior art date
Application number
PCT/EP2009/007130
Other languages
German (de)
French (fr)
Other versions
WO2010051890A8 (en
WO2010051890A2 (en
Inventor
Michael Hill
Martin Sicken
Original Assignee
Clariant Finance (Bvi) Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Clariant Finance (Bvi) Limited filed Critical Clariant Finance (Bvi) Limited
Priority to EP09778833A priority Critical patent/EP2352739A2/en
Priority to JP2011533573A priority patent/JP2012507481A/en
Priority to CN2009801401497A priority patent/CN102177169A/en
Priority to US13/125,365 priority patent/US20110224340A1/en
Publication of WO2010051890A2 publication Critical patent/WO2010051890A2/en
Publication of WO2010051890A3 publication Critical patent/WO2010051890A3/en
Publication of WO2010051890A8 publication Critical patent/WO2010051890A8/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K21/00—Fireproofing materials
    • C09K21/06—Organic materials
    • C09K21/12—Organic materials containing phosphorus
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/302—Acyclic unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/32—Esters thereof
    • C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/3217—Esters of acyclic unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Fireproofing Substances (AREA)
  • Detergent Compositions (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Epoxy Resins (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Artificial Filaments (AREA)

Abstract

The invention relates to a method for producing mono-vinylfunctionalized dialkylphosphinic acids, esters, and salts, characterized in that a) a phosphinic acid source (I) is converted with olefins (IV) to an alkylphosphonic acid, salt, or ester (II) in the presence of a catalyst A, b) the alkylphosphonic acid, salt, or ester (II) thus created is converted with acetylenic compounds of formula (V) into a mono-vinylfunctionalized dialkylphosphinic acid derivative (III) in the presence of a catalyst B, where R1, R2, R3, R4, R5, R6 are the same or different and are, independent of each other, among other things, H, C1-C-18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl, and X stands for H, C1-C-18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl, Mg, Ca, AI, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonized nitrogen base, and the catalysts A and B are transition metals and/or transition metal compounds and/or catalyst systems comprised of a transition metal and/or a transition metal compound and at least one ligand.
PCT/EP2009/007130 2008-11-06 2009-10-06 Method for producing mono-vinylfunctionalized dialkylphosphinic acid, salts and esters thereof, and the use thereof WO2010051890A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP09778833A EP2352739A2 (en) 2008-11-06 2009-10-06 Method for producing mono-vinylfunctionalized dialkylphosphinic acid, salts and esters thereof, and the use thereof
JP2011533573A JP2012507481A (en) 2008-11-06 2009-10-06 Process for the production of monovinyl-functional dialkylphosphinic acids, their salts and esters and their use
CN2009801401497A CN102177169A (en) 2008-11-06 2009-10-06 Method for producing mono-vinylfunctionalized dialkylphosphinic acid, salts and esters thereof, and the use thereof
US13/125,365 US20110224340A1 (en) 2008-11-06 2009-10-06 Method for Producing Mono-Vinylfunctionalized Dialkylphosphinic Acids, Salts and Esters Thereof, and the Use Thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102008056235.1 2008-11-06
DE102008056235A DE102008056235A1 (en) 2008-11-06 2008-11-06 Process for the preparation of monovinyl-functionalized dialkylphosphinic acids, their salts and esters and their use

Publications (3)

Publication Number Publication Date
WO2010051890A2 WO2010051890A2 (en) 2010-05-14
WO2010051890A3 true WO2010051890A3 (en) 2010-07-01
WO2010051890A8 WO2010051890A8 (en) 2010-11-25

Family

ID=41278681

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2009/007130 WO2010051890A2 (en) 2008-11-06 2009-10-06 Method for producing mono-vinylfunctionalized dialkylphosphinic acid, salts and esters thereof, and the use thereof

Country Status (6)

Country Link
US (1) US20110224340A1 (en)
EP (1) EP2352739A2 (en)
JP (1) JP2012507481A (en)
CN (1) CN102177169A (en)
DE (1) DE102008056235A1 (en)
WO (1) WO2010051890A2 (en)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5619756B2 (en) 2008-11-05 2014-11-05 クラリアント・ファイナンス・（ビーブイアイ）・リミテッド Process for the production of dialkylphosphinic acids, -esters and -salts using alkyl alcohol / acrolein and their use
DE102008055914A1 (en) 2008-11-05 2010-05-06 Clariant International Limited A process for the preparation of mono-hydroxy-functionalized dialkylphosphinic acids, esters and salts by means of acroleins and their use
DE102008056341A1 (en) 2008-11-07 2010-05-12 Clariant International Limited Process for the preparation of mono-amino-functionalized dialkylphosphinic acids, esters and salts by means of acrylonitriles and their use
EP2352740B1 (en) * 2008-11-07 2014-09-24 Clariant Finance (BVI) Limited Method for producing dialkylphosphinic acids and esters and salts thereof by means of acrylic acid derivatives and use thereof
DE102008056342A1 (en) 2008-11-07 2010-05-12 Clariant International Limited Process for the preparation of dialkylphosphinic acids, esters and salts by means of acrylonitriles and their use
US8772519B2 (en) * 2008-11-11 2014-07-08 Clariant Finance (Bvi) Limited Process for preparing mono-allyl-functionalized dialkylphosphinic acids, salts and esters thereof with allylic compounds, and the use thereof
DE102008060035A1 (en) 2008-12-02 2010-06-10 Clariant International Limited Process for the preparation of monohydroxy-functionalized dialkylphosphinic acids, esters and salts by means of vinyl esters of a carboxylic acid and their use
DE102008060535A1 (en) 2008-12-04 2010-06-10 Clariant International Limited Process for the preparation of mono-carboxy-functionalized dialkylphosphinic acids, esters and salts by means of vinyl ethers and their use
US9181487B2 (en) 2008-12-18 2015-11-10 Clariant Finance (Bvi) Limited Process for preparing ethylenedialkylphosphinic acids, esters and salts by means of acetylene and use thereof
DE102008063642A1 (en) 2008-12-18 2010-06-24 Clariant International Limited Process for the preparation of monocarboxy-functionalized dialkylphosphinic acids, esters and salts by means of alkylene oxides and their use
DE102008063668A1 (en) 2008-12-18 2010-07-01 Clariant International Limited Process for the preparation of alkylphosphonic acids, esters and salts by oxidation of alkylphosphonous acids and their use
DE102008063627A1 (en) 2008-12-18 2010-06-24 Clariant International Limited Process for the preparation of monohydroxy-functionalized dialkylphosphinic acids, esters and salts by means of ethylene oxide and their use
DE102008064003A1 (en) 2008-12-19 2010-06-24 Clariant International Limited Process for the preparation of monofunctionalized dialkylphosphinic acids, esters and salts and their use
DE102015223432A1 (en) * 2015-11-26 2017-06-01 Clariant International Ltd Polymeric flame retardant mixtures
KR102626451B1 (en) * 2017-07-20 2024-01-19 다우 실리콘즈 코포레이션 Method for preparing platinum organosiloxane complex

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2344332A1 (en) * 1973-09-03 1975-03-27 Hoechst Ag Vinyl-alkyl(aralkyl, aryl)-phosphinic acid prodn. - be heating 2-hydroxyethyl-alkyl(aralkyl, aryl)-phosphinic acid and removing water
EP0085391A1 (en) * 1982-01-29 1983-08-10 Meiji Seika Kaisha Ltd. Phosphinic acid derivatives and process for preparing the same
EP1369422A1 (en) * 2001-02-14 2003-12-10 Japan Science and Technology Corporation Process for preparation of alkenylphosphine oxides or alkenylphosphinic acid esters
EP1905776A1 (en) * 2006-09-28 2008-04-02 Clariant International Ltd. Asymmetrical substituted phosphine acids

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19828863C1 (en) * 1998-06-29 1999-09-02 Clariant Gmbh Production of phosphinate esters, useful as reactive fire retardants for thermoplastics and thermosetting resins and also as synthetic intermediates
DE19923617C2 (en) * 1999-05-25 2001-10-31 Clariant Gmbh Process for the preparation of phosphinic acid esters
DE19923619C2 (en) * 1999-05-25 2001-08-23 Clariant Gmbh Process for the preparation of dialkylphosphinic acids and their salts

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2344332A1 (en) * 1973-09-03 1975-03-27 Hoechst Ag Vinyl-alkyl(aralkyl, aryl)-phosphinic acid prodn. - be heating 2-hydroxyethyl-alkyl(aralkyl, aryl)-phosphinic acid and removing water
EP0085391A1 (en) * 1982-01-29 1983-08-10 Meiji Seika Kaisha Ltd. Phosphinic acid derivatives and process for preparing the same
EP1369422A1 (en) * 2001-02-14 2003-12-10 Japan Science and Technology Corporation Process for preparation of alkenylphosphine oxides or alkenylphosphinic acid esters
EP1905776A1 (en) * 2006-09-28 2008-04-02 Clariant International Ltd. Asymmetrical substituted phosphine acids

Non-Patent Citations (15)

* Cited by examiner, † Cited by third party
Title
BRAVO-ALTAMIRANO ET AL: "A novel approach to phosphonic acids from hypophosphorous acid", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 48, no. 33, 19 July 2007 (2007-07-19), pages 5755 - 5759, XP022163552, ISSN: 0040-4039 *
DATABASE BEILSTEIN [online] BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; March 2009 (2009-03-01), Database accession no. Reaction ID 1917638, 1915900 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1979, GAREEV, R. D. ET AL: "Stereochemistry of a 1,3-dipolar cycloaddition of diazomethane to .alpha.-substituted vinylphosphoryl compounds containing a chiral phosphorus atom", XP002567581, retrieved from STN Database accession no. 1979:404894 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1984, RAEVSKII, O. A. ET AL: "Electron-donor and acceptor functions of physiologically active and model compounds. V. Calculation of the electron-donor function of phosphoryl oxygen", XP002567582, retrieved from STN Database accession no. 1984:6676 *
ISABELLE ABRUNHOSA-THOMAS ET AL: "Alkylation of H-Phosphinate Esters under Basic Conditions", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, EASTON.; US, vol. 72, no. 8, 1 January 2007 (2007-01-01), pages 2851 - 2856, XP002530192, ISSN: 0022-3263, [retrieved on 20070313] *
M. I. KABACHNIK, T. YA. MEDVED, I. B. GORYUNOVA, L. I. TIKHONOVA AND E. I. MATROSOV: "Synthesis and properties of some ethylenediphosphoryl compounds", RUSSIAN CHEMICAL BULLETIN, vol. 23, no. 10, 1974, XP002557075 *
MONTCHAMP J L: "Recent advances in phosphorus-carbon bond formation: synthesis of H-phosphinic acid derivatives from hypophosphorous compounds", JOURNAL OF ORGANOMETALLIC CHEMISTRY, ELSEVIER-SEQUOIA S.A. LAUSANNE, CH, vol. 690, no. 10, 16 May 2005 (2005-05-16), pages 2388 - 2406, XP004877374, ISSN: 0022-328X *
NIFANT'EV E E ET AL: "Reactions of acetylenes with hypophosphorous and phosphonous acids", JOURNAL OF GENERAL CHEMISTRY USSR, CONSULTANTS BUREAU, NEW YORK, NY, US, vol. 56, no. 4, 20 September 1986 (1986-09-20), pages 680 - 688, XP002165520, ISSN: 0022-1279 *
PATRICE RIBIÈRE ET AL: "NiCl2-Catalyzed Hydrophosphinylation", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, EASTON.; US, vol. 70, no. 10, 1 January 2005 (2005-01-01), pages 4064 - 4072, XP002530191, ISSN: 0022-3263 *
RUFLIN CATHERINE ET AL: "Tetrakis(trimethysilyl)hypophosphate P2O2(OTMS)4: Synthesis, reactivity and application as flame retardant", HETEROATOM CHEMISTRY, VCH PUBLISHERS, DERFIELD BEACH, FL, US, vol. 18, no. 7, 6 November 2007 (2007-11-06), pages 721 - 731, XP009118331, ISSN: 1042-7163 *
SARATOVSKIKH I V ET AL: "Phosphorus-containing Aminocarboxylic Acids: XIV. Synthesis of Analogs of [alpha]-Substituted Glutamic Acid", RUSSIAN JOURNAL OF GENERAL CHEMISTRY, NAUKA/INTERPERIODICA, MO, vol. 75, no. 7, 1 July 2005 (2005-07-01), pages 1077 - 1084, XP019301159, ISSN: 1608-3350 *
SYLVINE DEPRÈLE ET AL: "Environmentally Benign Synthesis of H-Phosphinic Acids Using a Water-Tolerant, Recyclable Polymer-Supported Catalyst", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 6, no. 21, 1 January 2004 (2004-01-01), pages 3805 - 3808, XP002500861, ISSN: 1523-7060, [retrieved on 20040918] *
SYLVINE DEPRÈLE ET AL: "Palladium-Catalyzed Hydrophosphinylation of Alkenes and Alkynes", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC. US, vol. 124, no. 32, 1 January 2002 (2002-01-01), pages 9387, XP002500862, ISSN: 0002-7863 *
ZHURNAL OBSHCHEI KHIMII , 49(3), 493-503 CODEN: ZOKHA4; ISSN: 0044-460X, 1979 *
ZHURNAL OBSHCHEI KHIMII , 53(8), 1724-8 CODEN: ZOKHA4; ISSN: 0044-460X, 1983 *

Also Published As

Publication number Publication date
WO2010051890A8 (en) 2010-11-25
JP2012507481A (en) 2012-03-29
EP2352739A2 (en) 2011-08-10
US20110224340A1 (en) 2011-09-15
DE102008056235A1 (en) 2010-05-12
WO2010051890A2 (en) 2010-05-14
CN102177169A (en) 2011-09-07

Similar Documents

Publication Publication Date Title
WO2010051890A8 (en) Method for producing mono-vinylfunctionalized dialkylphosphinic acid, salts and esters thereof, and the use thereof
WO2010051887A8 (en) Method for producing dialkylphosphinic acids and esters and salts thereof by means of vinyl compounds and use thereof
WO2010069545A3 (en) Process for preparing ethylenedialkylphosphinic acids, esters and salts by means of acetylene and use thereof
WO2011134620A3 (en) Method for producing mixtures of alkylphosphonous acid salts and dialkylphosphinic acid salts
WO2011134621A3 (en) Method for producing alkylphosphonous acid salts
JP2012507481A5 (en)
TW480267B (en) Process for preparing salts of dialkylphosphinic acids
US8097747B2 (en) Process for the alkylation of phosphorus-containing compounds
EP1500676A3 (en) Flame-resistant polyamide
MX2019002659A (en) Flame retardant-stabilizer combination for thermoplastic polymers.
EP1454949A3 (en) Flame retardant dispersion
EP1477520A3 (en) Halogenated flame retardant combination
MY194031A (en) Flame retardant-stabilizer combination for thermoplastic polymers
EP2145894A3 (en) Salts of diorganyl phosphinic acids, method for their manufacture and their application
JP2012507476A5 (en)
DE59906738D1 (en) Process for the preparation of phosphinic acid esters
ATE266628T1 (en) METHOD FOR CARBONYLATING PENTENENITRILE
JP2011527381A5 (en)
AU1338999A (en) Method for producing dialkylphosphinic acid salts
AU2003230587A1 (en) Bisphosphite ligands for carbonylation processes
GB1162465A (en) Metal Derivatives of Alkylhydroxyphenylalkyphosphinic Acids
IN2015DN01081A (en)
JPH0665589A (en) Water-soluble cutting oil composition
Herrmann et al. The crystal and molecular structure of the ammonium bismuth citrate dihydrate [(NH4)+ Bi (C6H4O7)−]· 2H2O
RU2014133183A (en) METHOD FOR PRODUCING ETHYLENE-unsaturated CARBONIC ACIDS OR THEIR ETHERS AND THE CATALYST FOR THIS

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 200980140149.7

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 09778833

Country of ref document: EP

Kind code of ref document: A2

WWE Wipo information: entry into national phase

Ref document number: 2009778833

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 13125365

Country of ref document: US

WWE Wipo information: entry into national phase

Ref document number: 2011533573

Country of ref document: JP